Fryman was 25 years old when he signed with the Pittsburgh Pirates in 1965. He debuted out of the bullpen for the Pirates in 1966, however, made more appearances as a starter, and was used pretty evenly in both roles throughout his career. He went 12-9 with a 3.81 earned run average his rookie season, including three shutouts in a row against the Philadelphia Phillies, New York Mets and Chicago Cubs, respectively. His shutout against the Mets was nearly a perfect game, as Ron Hunt led off the Mets\' half of the first inning with a single, and was immediately caught trying to steal second. Fryman retired the next 26 batters he faced without allowing another baserunner all game.\n', '

His record dipped to 3-8 with a 4.05 ERA in 1967. Following the season, he was dealt to the Philadelphia Phillies with Bill Laxton, Don Money and Harold Clem for Jim Bunning.\n', '

After a complete game victory against the San Francisco Giants on June 18, Fryman\'s record stood at 10-5 with a 1.61 ERA, and he was named the Phillies\' sole representative at the 1968 All-Star Game. He dropped his next five decisions, and ended the season with a 12-14 record and 2.78 ERA.\n', '

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